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The D Word: Can the Cubs Repeat, and Repeat, and Repeat?

It’s been 17 years since any ball club won two World Series in a row. These Cubs know how to break droughts—but can they build a dynasty?

Four of the Cubs young stars celebrate winning the National League Championship Series in 2016.   Photo: Nuccio DiNuzzo/Chicago Tribune

Late in the evening of October 26, 17 years ago this fall, a baseball, brilliantly white and spinning so astonishingly fast against the sky that its red laces were scarcely visible, arced majestically through the dark New York City night before settling, with a quiet thump, into the waiting glove of Bernie Williams.

That baseball, secured in that moment, clinched an extraordinary third consecutive World Series championship for Williams’s New York Yankees, and a fourth in five seasons. And since that night, baseball has yet to see another team like it—has yet to see, in fact, even another repeat champion.

Until, perhaps, this year.

You may know that the Chicago Cubs won a World Championship last year. There were a few stories in the paper. But you may not know that Theo Epstein’s ballclub, victors of 103 games last year and 200 in the last two seasons alone—both the best marks in baseball—is as well-positioned as any team of the last two decades to become what no other squad has been since the turn of the century: a dynasty.

To wit: The Cubs have some of the best players in baseball. The Cubs have some of the youngest players in baseball. The Cubs have some of the cheapest players in baseball. And the Cubs have some players who are, perhaps, none of those three things, but still better at what they do than the equivalent players on other teams. And there’s more on the way.

Let’s start with the first claim: that the Cubs have some of the best players in baseball. This one’s pretty simple to establish. If you look at the Cubs’ cumulative Wins Above Replacement for 2017—that’s a statistic that attempts to roll all of a baseball players’ contributions on the field into a single number, with some success—you’ll find that just one team, the Los Angeles Dodgers, bests the North Siders’ current projected mark of 49.2, which translates to about 94 expected wins.

But even that number undersells the Cubs’ talent. If you strip out all but the top five players on every team—basically, testing how good the Cubs’ best players are, compared to other teams’ best—the Dodgers drop from first to fourth, and the Cubs stay in second (behind the Washington Nationals). Do the opposite, and look at only a team’s other 20 players—the backups and second stringers—and the Cubs once again stay in second, with the Dodgers ahead of them and the Nationals tumbling to 13th. In short: The Cubs’ stars are better than just about anyone else’s, and the Cubs’ scrubs are better than just about anyone else’s, too. And that’s true of nobody else.        

But just having good players is not enough to create a dynasty. Any old franchise can pull its resources together for a single season, spend wildly in free agency, and look good for a little while. That’s no recipe for sustained success. For that, you need players young enough that they can age into their prime years together, and cheap enough that you can afford to keep them all together. And the Cubs, more than any other team in the league, have just that.

There’s Kris Bryant, who just won the National League MVP award at age 24. There’s Anthony Rizzo, the Cubs’ clubhouse leader, who finished just behind Bryant in MVP voting at age 26. Javier Báez, the team’s electric jack-of-all trades, is just 24. Kyle Schwarber, the bull-headed slugger who established himself as an October legend last fall with an improbable World Series comeback, is the same age. Addison Russell, the All-Star, is 23. Jason Heyward is 27. Willson Contreras is 25. The Cubs clubhouse holds a constellation of stars, the likes of which the game hasn’t really seen since, yes, those New York Yankees started winning championships back in the late 1990s.

And, thanks to baseball’s service time rules, which are deeply unfriendly to labor, every single one of those young men is signed, for what amounts to cents on the dollar, through 2021. Sure, the Cubs will have to spend some money, perhaps as soon as this offseason, to bring in more veteran pitching to supplement what they already have. But they’ll do it with pleasure, because, by drafting or signing so many of these young players a half-decade ago, they’ll have one of the game’s all-time great core lineups for a half-decade more without paying the full cost of their talents.

It’s OK to feel a little icky about a labor system that forces young men to settle for less than what they’re worth (none of them are free to negotiate with other teams, until they reach free agency), while still watching all those talents on display on the same legendary field. Not since Jordan and Pippen roamed the hardcourt on the West Side has Chicago had such generational talents in town, and not since the Blackhawks entered the era they’re now exiting has a Chicago franchise had so much promise for its future.

Those Blackhawks teams managed three Stanley Cups with their current core, and that’s a reasonably good place to set the over-under for this Cubs team, too. They’ve already got one ring in the bag, after all, and they probably have five more shots at it with this group. That’s no guarantee of anything, of course—winning a championship is incredibly, back-breakingly hard, and takes a good measure of luck besides—but the fact that we can even reasonably talk about the chance for three titles for the Cubs is astonishing. Now, the Cubs begin their charge to make that future a reality. A dynasty has never been so close at hand.

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